US3112159A - Process for preparing dye-receptive polyolefin fibres - Google Patents

Process for preparing dye-receptive polyolefin fibres Download PDF

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US3112159A
US3112159A US34385A US3438560A US3112159A US 3112159 A US3112159 A US 3112159A US 34385 A US34385 A US 34385A US 3438560 A US3438560 A US 3438560A US 3112159 A US3112159 A US 3112159A
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acid
fibres
dyes
polyolefin
receptive
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Cappuccio Vittorio
Riboni Ubaldo
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Montedison SpA
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/79—Polyolefins
    • D06P3/791—Polyolefins using acid dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
    • D01F11/04—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers
    • D01F11/06—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/46—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyolefins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/928—Polyolefin fiber

Definitions

  • Another object is to provide a method of treating crystalline polyolefins whereby their affinity for acid dyes is markedly increased.
  • textile fibres from a crystalline polyolcfin and having unusual receptivity for dyes, and particularly for acid dyes can be obtained by mixing the polyolefin with a dicarboxylic acid or derivative thereof.
  • the dicarboxylic acid may be aliphatic, aromatic, or alicyclic, and may be either saturated or unsaturated.
  • the mixture is then spun and, in accordance with another aspect of our invention, may be subjected to the action of an amino or imino compound.
  • non-aminated fibres are dyeable with either dispersed acetate dyes or basic dyes.
  • Particularly suitable dicarboxylic acids and/or acid anhydrides include succinic acid, sebacic acid, adipic acid, azelaic acid, glutaric acid, pimelic acid, suberic acid, nonanedicarboxylic acid, decanedicarboxylic acid, fumaric acid, maleic acid (and maleic anhydride) and phthalic acid (and anhydride).
  • a small amount of a solid dispersant can be mixed with the polyolefin, as described in Italian patent application No. 8529/60 filed on February 15, 1960.
  • Such dispersants include cetyl and stearic alcohols; stearic and terephthalic acids; benzoin; furoin; vinyl stearate; mono-, di-
  • tri-stearic esters of glycerol mono-ethanolamine stearate; stearic acid amide; N-diethanoi-lauramide', C C aliphatic amines; condensation products of ethylene oxide with alcohols, amines and phenols; polyacrylonitrile; polystyrene; styrene copolymers; terpcnc polymers; etc.
  • the dicarboxylic compounds may be added to the polyolcfin in an amount from about 1 to 25% by weight of the mixture.
  • the solid dispersant should be present in an amount from about 0.1 to 5% by weight of the mixture.
  • the amination of the fibres is preferably carried out by treating the fibres with an anhydrous amine or imine, or with a boiling (generally aqueous) solution of the amine or imino for a time varying from a few seconds to two to three hours, depending on the reactivity of the amine or imiue used.
  • Typical amines and imines that are suitable include ethylene diarnine, propylene diamine, hexamethylene diamine, triethylene diamine, diethylene triamine, tetraethylene pentarnine, ethylene imine. polyethylene imine. 3-diethylaniino-Npropylamine, tetramethylene diamine, and cyclohexylamine.
  • the spinning of the polyolefin-dicarboxylic acid composition is carried out more easily than the spinning of the polyolefin alone.
  • the presence of the dicarboxylic compound occasionally makes it possible to carry out the extrusion at lower temperatures.
  • FIGURE shows a schematic representation of the process of the present invention.
  • polyolefins referred to in same examples are preferably those prepared with Nattas catalysts as described, for example, in Italian Patent 526,101 and US. Patent No. 3,014,016.
  • the heptane residue indicates the presence of isotactic polypropylene macromolecules.
  • the crystallinity of the polypropylenes of the working examples is due to the presence of isotactic macromolecules.
  • Example 1 A mix is prepared in a Werner mixer from 9 kg. of polypropylene and 1 kg. maleic anhydride at room temperature.
  • the polypropylene is characterized by the following: intrinsic viscosity [1 1.4 (determined in tetrahydronaphthalene at 135 (3.); residue after heptane extraction 97%; ash content 0.055%.
  • the mix is spun in a melt spinning ning head temperature of 230 C.
  • the fibres are stretched with a ratio of 1:5 at C., are cut, and the staple is aminated by treatment with a boiling 4.5% aqueous ethyleneimine solution for 30 minutes, with a fibre/bath ratio (by weight) of 1:15.
  • the staple is then washed and dried.
  • a mix is prepared in a Werner apparatus at room temperature from 9 kg. polypropylene, 0.8 kg. maleic anhydride, and 0.2 kg. stearic acid dispersant, which facilitates dispersion of the maleic anhydride in the molten mass.
  • the polypropylene used exhibits the following oharacteristics: intrinsic viscosity [1 1.4; residue after heptane extraction 97%; ash content 0.55%.
  • the mix is spun in a melt spinning device at a spin- Example 3
  • a mix is prepared in a ball mill from 94.5 g. polypropylene, 1.5 g. adipic acid, and 4 g. maleic anhydride.
  • the polypropylene exhibits the following characteristics: In] 0.96, residue after hcptane extraction 94%, ash eon tent 0.21%.
  • This mix is spun in a laboratory melt spinning device at 215 C.
  • the fibres are stretched with a ratio of 1:6.5 at 130 C., are aminated by treatment with a boiling 20% aqueous tetraethylene pentaminc solution for 60 minutes with a fibre/bath ratio of 1:10, are washed with water, and are then dried.
  • Example 4 A mix is prepared in a ball mill from 90 g. polypropylene and 10 g. of phthalic anhydride.
  • the polypropylene exhibits the following characteristics: [1;] 096, residue after heptane extraction 94%, ash content 0.21%.
  • Example 4A After amination of undyed fibres prepared as described in Example 4, this amination being carried out as described in Example 1, solid intense shades are obtained on these fibres with the following four acid dyes: solid yellow 26, wool red 13, alizarine blue ACF, and acid black IVS.
  • Example 5 A mix is prepared in a ball mill from 90 g. polypropylene and g. sebacic acid.
  • the polypropylene exhibits the following characteristics: [1;] 0.96, residue after heptane extraction 94%, ash content 0.21%.
  • This mix is spun in a laboratory melt spinning device at 210 C.
  • the fibres are stretched with a ratio of 1:5 at 130 C. They are then aminated by treatment with a 50% aqueous tetramethylene diamine solution for 2 hours with a fibre/bath ratio of 1:10. They are then washed and dried. with the following four acid dyes: solid yellow 26, wool red B, alizarine blue ACF, and acid black IVS.
  • a method for rendering polyolefins receptive to dyes comprising melt-mixing said polyolefin with Intense solid shades are produced on these fibres a dicarboxylic acid type compound selected from the group consisting of dicarboxylic acids and dicarboxylic acid anhydrides and extruding the mixture to form fibres.
  • polyolefin is polypropylene consisting prevailingly of isotactic macromolecules.
  • the dicarboxylic compound is selected from the group consisting of succinic acid, sebacic acid, adipic acid, azelaic acid, glutaric acid, pimclie acid, suberie acid, nonanediearboxylic acid, deeanedicarboxylic acid, fumaric acid, maleic acid, phthalic acid, maleic anhydride, phthalic anhydride, and mixtures thereof.
  • the amine is selected from the group consisting of ethylene amine, propylenediamine, hexamethylene diamine, trimethylene diarnine, diethylene triaminc, tetraethylene pentamine, 3- diethylamino-N-propylamine, tetramethylene diamine, and cyclhexylamine.
  • the imine is selected from the group consisting of ethyleneimine and polyethyleneimine.
  • Datyncr Man-Made Textiles, May 1946, Dyeing and Finishing Sec, pp. 63-65.

Description

Nov. 26, 1963 v. CAPPUCCIO ETAL 3,112,159
PROCESS FOR PREPARING DYE-RECEPTIVE POLYOLEFIN FIBRES Filed June 7, 1960 DICARBOXYLIC ACID COMPOUND POLYOLEF IN DlSPERSANT SPINNING I STRETCH! NG AMINATION DYE-RECEPTIVE FIBER INVENTORS VITTORIO N CAPPUCCIO BY UBALDO RIBONI ATTORNE y United States Patent PROCESS FOR PREPARING DYE-RECEPTIVE POLYOLEFIN FiBREf-i Vittorio Cappuccio and Uhaldo Riboni, Terni, Italy, assignors to Montecatini, Societa Generale per llndustria Mineraria e Chimica, Milan, Italy, a corporation of Italy Filed June 7, 1960, Ser. No. 34,385 Claims priority, application Italy June 9, 1959 11 Claims. (Cl. 1854) The present invention relates to crystalline polyolefin fibres that are particularly receptive to dyes and to a process for preparing the same.
Various processes for the obtaining of textile fibres from crystalline polyolefins, which fibres have a particular receptivity for dyes, have been described. Four typical prior processes may be summarized as follows:
(1) Preparation of fibres from mixtures: Polyolefins are mixed with other resins (e.g., epoxy resins, polyamides, 'polyimines, polyesters and the like) capable of rendering the fibres dyeable, and the mixtures thus obtained are spun according to the normal spinning techniques. When an epoxy resin is used as a component of the mixture, a subsequent treatment of the resulting fibres with a basic substance is provided for.
(2) Grafting of reactive monomers onto the fibres: The polyolefin fibres are treated with reactive monomers in the presence of agents which catalyze the polymerization of the monomers. These are thus bound onto the fibres by means of graft polymerization. Typical reactive monomers include vinyl monomers such as acrylonitrile, styrene, vinyl esters, nitrogen-containing monomers such as vinylpyridines, isopropenylpyridines, etc., and acid monomers.
(3) Mixing of polyolefins with various monomers in the spinning stage: Polyolefins are mixed with vinyl monomers, acid monomers, or the like before spinning, and the mixes are then subjected to the usual technological operations for preparing textile fibres.
(4) Chemical treatments on the fibres: Polyolefin fibres are subjected to sulfonation and the sulfonated fibres are treated with amines.
It is an object of this invention to provide a novel method for rendering crystalline polyolefins dye-receptive.
Another object is to provide a method of treating crystalline polyolefins whereby their affinity for acid dyes is markedly increased.
Additional objects will become apparent hereinafter.
We have now found that textile fibres from a crystalline polyolcfin and having unusual receptivity for dyes, and particularly for acid dyes, can be obtained by mixing the polyolefin with a dicarboxylic acid or derivative thereof. The dicarboxylic acid may be aliphatic, aromatic, or alicyclic, and may be either saturated or unsaturated. The mixture is then spun and, in accordance with another aspect of our invention, may be subjected to the action of an amino or imino compound. However, non-aminated fibres are dyeable with either dispersed acetate dyes or basic dyes.
Particularly suitable dicarboxylic acids and/or acid anhydrides include succinic acid, sebacic acid, adipic acid, azelaic acid, glutaric acid, pimelic acid, suberic acid, nonanedicarboxylic acid, decanedicarboxylic acid, fumaric acid, maleic acid (and maleic anhydride) and phthalic acid (and anhydride).
In addition to the dicarboxylic compound a small amount of a solid dispersant can be mixed with the polyolefin, as described in Italian patent application No. 8529/60 filed on February 15, 1960. Such dispersants include cetyl and stearic alcohols; stearic and terephthalic acids; benzoin; furoin; vinyl stearate; mono-, di-
and tri-stearic esters of glycerol; mono-ethanolamine stearate; stearic acid amide; N-diethanoi-lauramide', C C aliphatic amines; condensation products of ethylene oxide with alcohols, amines and phenols; polyacrylonitrile; polystyrene; styrene copolymers; terpcnc polymers; etc.
The dicarboxylic compounds may be added to the polyolcfin in an amount from about 1 to 25% by weight of the mixture. The solid dispersant should be present in an amount from about 0.1 to 5% by weight of the mixture.
The amination of the fibres (now consisting of polyolefin-dicarboxylic compound mixture) is preferably carried out by treating the fibres with an anhydrous amine or imine, or with a boiling (generally aqueous) solution of the amine or imino for a time varying from a few seconds to two to three hours, depending on the reactivity of the amine or imiue used.
Typical amines and imines that are suitable include ethylene diarnine, propylene diamine, hexamethylene diamine, triethylene diamine, diethylene triamine, tetraethylene pentarnine, ethylene imine. polyethylene imine. 3-diethylaniino-Npropylamine, tetramethylene diamine, and cyclohexylamine.
The spinning of the polyolefin-dicarboxylic acid composition is carried out more easily than the spinning of the polyolefin alone. The presence of the dicarboxylic compound occasionally makes it possible to carry out the extrusion at lower temperatures.
The attached FIGURE shows a schematic representation of the process of the present invention.
The following examples will further illustrate our in vention; the polyolefins referred to in same examples are preferably those prepared with Nattas catalysts as described, for example, in Italian Patent 526,101 and US. Patent No. 3,014,016.
As is known to the art subsequent to the discoveries of Natta et al., and as will be noted from the following examples, the heptane residue indicates the presence of isotactic polypropylene macromolecules. Thus, the crystallinity of the polypropylenes of the working examples is due to the presence of isotactic macromolecules.
All parts are by weight unless otherwise stated.
Example 1 A mix is prepared in a Werner mixer from 9 kg. of polypropylene and 1 kg. maleic anhydride at room temperature. The polypropylene is characterized by the following: intrinsic viscosity [1 1.4 (determined in tetrahydronaphthalene at 135 (3.); residue after heptane extraction 97%; ash content 0.055%.
The mix is spun in a melt spinning ning head temperature of 230 C. The fibres are stretched with a ratio of 1:5 at C., are cut, and the staple is aminated by treatment with a boiling 4.5% aqueous ethyleneimine solution for 30 minutes, with a fibre/bath ratio (by weight) of 1:15. The staple is then washed and dried.
On these fibres intense and solid shades are obtained with the following four dyes of the acid type: solid yellow 2G, wool red B, alizarine blue ACF, and acid black IVS.
device at a spin- Example 2 A mix is prepared in a Werner apparatus at room temperature from 9 kg. polypropylene, 0.8 kg. maleic anhydride, and 0.2 kg. stearic acid dispersant, which facilitates dispersion of the maleic anhydride in the molten mass. The polypropylene used exhibits the following oharacteristics: intrinsic viscosity [1 1.4; residue after heptane extraction 97%; ash content 0.55%.
The mix is spun in a melt spinning device at a spin- Example 3 A mix is prepared in a ball mill from 94.5 g. polypropylene, 1.5 g. adipic acid, and 4 g. maleic anhydride. The polypropylene exhibits the following characteristics: In] 0.96, residue after hcptane extraction 94%, ash eon tent 0.21%. This mix is spun in a laboratory melt spinning device at 215 C. The fibres are stretched with a ratio of 1:6.5 at 130 C., are aminated by treatment with a boiling 20% aqueous tetraethylene pentaminc solution for 60 minutes with a fibre/bath ratio of 1:10, are washed with water, and are then dried.
On these fibres intense solid shades are produced with the following four dyes: solid yellow 26, wool red B, alizarine blue ACF, and acid black lVS.
Example 4 A mix is prepared in a ball mill from 90 g. polypropylene and 10 g. of phthalic anhydride. The polypropylene exhibits the following characteristics: [1;] 096, residue after heptane extraction 94%, ash content 0.21%.
This mix is spun in a laboratory melt spinning device at 210 C. The fibres are stretched with a ratio of 1:7 at 130 C. Intense solid shades are obtained by dyeing with the following dispersed acetate dyes and basic dyes: Setacyl yellow 36, Cibacet scarlet BR, Acetoquinone blue RHO, crystals malachite green, basic fuchsine, and Astrazon blue.
Example 4A After amination of undyed fibres prepared as described in Example 4, this amination being carried out as described in Example 1, solid intense shades are obtained on these fibres with the following four acid dyes: solid yellow 26, wool red 13, alizarine blue ACF, and acid black IVS.
Example 5 A mix is prepared in a ball mill from 90 g. polypropylene and g. sebacic acid. The polypropylene exhibits the following characteristics: [1;] 0.96, residue after heptane extraction 94%, ash content 0.21%. This mix is spun in a laboratory melt spinning device at 210 C. The fibres are stretched with a ratio of 1:5 at 130 C. They are then aminated by treatment with a 50% aqueous tetramethylene diamine solution for 2 hours with a fibre/bath ratio of 1:10. They are then washed and dried. with the following four acid dyes: solid yellow 26, wool red B, alizarine blue ACF, and acid black IVS.
Variations can, of course, be made without departing from the spirit of our invention.
Having thus described our invention, what we desire to secure and claim by Letters Patent is:
1. A method for rendering polyolefins receptive to dyes, this method comprising melt-mixing said polyolefin with Intense solid shades are produced on these fibres a dicarboxylic acid type compound selected from the group consisting of dicarboxylic acids and dicarboxylic acid anhydrides and extruding the mixture to form fibres.
2. The method of claim 1, wherein the polyolefin is polypropylene consisting prevailingly of isotactic macromolecules.
3. The method of claim 1, wherein the mixture comprises from about to 99% of polyolefin and from about 25 to 1% of dicarboxylic acid type compound.
4. The method of claim 1, wherein the dicarboxylic compound is selected from the group consisting of succinic acid, sebacic acid, adipic acid, azelaic acid, glutaric acid, pimclie acid, suberie acid, nonanediearboxylic acid, deeanedicarboxylic acid, fumaric acid, maleic acid, phthalic acid, maleic anhydride, phthalic anhydride, and mixtures thereof.
5. The method of claim 1, wherein there is added to the mixture at small proportion of a solid dispersant for the dicarboxylic compound.
6. The method of claim 1, wherein the fibres are subiected to a hot amination treatment.
7. The method of claim 6, wherein an amine is used for the hot amination.
8. The method of claim 6, wherein an imine is used for the hot amination.
9. The method of claim 7, wherein the amine is selected from the group consisting of ethylene amine, propylenediamine, hexamethylene diamine, trimethylene diarnine, diethylene triaminc, tetraethylene pentamine, 3- diethylamino-N-propylamine, tetramethylene diamine, and cyclhexylamine.
10. The method of claim 7, wherein the imine is selected from the group consisting of ethyleneimine and polyethyleneimine.
11. The method of claim 1, wherein the extruded fibres are hot-stretched with a ratio between 1:2 and 1:10, at a temperature of from about to C.
References Cited in the file of this patent UNITED STATES PATENTS 2,142,007 Schlack Dec. 27, 1938 2.219,700 Pcrrin et al. Oct. 29, 1940 2,306,880 Hcymann Dec. 29, 1942 2,327,705 Frolich Aug. 24, 1943 2,362,375 Hcymann Nov. 7, 1944 2,394,688 Heymann Feb. 12, 1946 2,646,339 Ward et a1 July 21, 1953 2,694,696 Melamcd Nov. 16, 1954 2,984,634 Caldwell et al. May 16, 1961 2,993,018 Steinlin July 18, 1961 3,011,860 Hirshfeld et at Dec. 5, 1961 3,013,998 Bottnglioli Dec. 19, 1961 FORETG N PATENTS 218,673 Australia Nov. 10, 1958 OTHER REFERENCES Gamble et al.: Amer. Dyestuff Reported April 14, 1952, pp. 1 223-227, particularly p. P225.
Datyncr: Man-Made Textiles, May 1946, Dyeing and Finishing Sec, pp. 63-65.

Claims (1)

1. A METHOD FOR RENDERING POLYOLEFINS RECEPTIVE TO DYES, THIS METHOD COMPRISING MELT-MIXING SAID POLYOLEFIN WITH A DICARBOXYLIC ACID TYPE COMPOUND SELECTED FROM THE GROUP CONSISTING OF DICARBOXYLIC ACIDS AND DICARBOXYLIC ACID ANHYDRIDES AND EXTRUDING THE MIXTURE TO FORM FIBRES.
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US3184281A (en) * 1962-02-02 1965-05-18 Asahi Chemical Ind Process for dyeing polyolefin articles
US3205156A (en) * 1961-03-23 1965-09-07 Toyo Rayon Co Ltd Method of preparing polyolefine and polystyrene graft copolymers having an alkylene imine bonded thereto
US3235623A (en) * 1961-01-02 1966-02-15 Rhodiaceta Polypropylene heat stabilized with interpolyamide
US3305603A (en) * 1963-09-23 1967-02-21 Ici Ltd Method of improving acid dyeability of fibre-forming polymers
US3310548A (en) * 1963-11-29 1967-03-21 Exxon Research Engineering Co Dyeable polyolefins
US3320334A (en) * 1956-12-12 1967-05-16 Montedison Spa Poly-alpha-olefin pyridinic polyamide compositions having high receptivity to dyestuffs
US3326826A (en) * 1963-09-04 1967-06-20 Exxon Research Engineering Co Dye receptive compositions comprising polyolefins and nitrogen-containing condensation polymers
US3364281A (en) * 1960-05-13 1968-01-16 Kureha Kasei Kabushiki Kaisha Dyeable crystalline polyolefin compositions
US3397032A (en) * 1960-07-28 1968-08-13 Ici Ltd Coloration of polyolefins
US3404140A (en) * 1963-09-30 1968-10-01 Toyo Rayon Co Ltd Shaped article of polyolefin composition having improved dyeability containing metalcompounds and a process for dyeing the same
US4124549A (en) * 1974-08-22 1978-11-07 Aicello Chemical Co., Ltd. Corrosion-inhibiting plastic films
US4263009A (en) * 1978-01-31 1981-04-21 Milliken Research Corporation Method for improving the dyeing characteristics of textile materials containing polyolefin fibers and products produced thereby
WO1996001916A1 (en) * 1994-07-12 1996-01-25 Lyondell Petrochemical Company Wettable polyolefin fiber compositions and method
WO1999020817A1 (en) * 1997-10-22 1999-04-29 Deutsche Institute für Textil- und Faserforschung Stuttgart Method for producing aqueous liquor dyeable modified polypropylene threads and the use thereof
WO2022077534A1 (en) * 2020-10-13 2022-04-21 广东永畅兴精密制造股份有限公司 Colored synthetic fiber and preparation method therefor

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US3317633A (en) * 1964-04-01 1967-05-02 Stevens & Co Inc J P Polyolefins of improved dye affinity modified with unsaturated polyester resins

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US2984634A (en) * 1957-01-30 1961-05-16 Eastman Kodak Co Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid
US2993018A (en) * 1958-01-28 1961-07-18 Files De Calais Production of coloured filaments, threads and the like from viscose
US3011860A (en) * 1958-09-10 1961-12-05 Chemstrand Corp Production of vinyl polymers containing a naphthol coupling component

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US3320334A (en) * 1956-12-12 1967-05-16 Montedison Spa Poly-alpha-olefin pyridinic polyamide compositions having high receptivity to dyestuffs
US3364281A (en) * 1960-05-13 1968-01-16 Kureha Kasei Kabushiki Kaisha Dyeable crystalline polyolefin compositions
US3397032A (en) * 1960-07-28 1968-08-13 Ici Ltd Coloration of polyolefins
US3235623A (en) * 1961-01-02 1966-02-15 Rhodiaceta Polypropylene heat stabilized with interpolyamide
US3205156A (en) * 1961-03-23 1965-09-07 Toyo Rayon Co Ltd Method of preparing polyolefine and polystyrene graft copolymers having an alkylene imine bonded thereto
US3184281A (en) * 1962-02-02 1965-05-18 Asahi Chemical Ind Process for dyeing polyolefin articles
US3326826A (en) * 1963-09-04 1967-06-20 Exxon Research Engineering Co Dye receptive compositions comprising polyolefins and nitrogen-containing condensation polymers
US3305603A (en) * 1963-09-23 1967-02-21 Ici Ltd Method of improving acid dyeability of fibre-forming polymers
US3404140A (en) * 1963-09-30 1968-10-01 Toyo Rayon Co Ltd Shaped article of polyolefin composition having improved dyeability containing metalcompounds and a process for dyeing the same
US3310548A (en) * 1963-11-29 1967-03-21 Exxon Research Engineering Co Dyeable polyolefins
US4124549A (en) * 1974-08-22 1978-11-07 Aicello Chemical Co., Ltd. Corrosion-inhibiting plastic films
US4263009A (en) * 1978-01-31 1981-04-21 Milliken Research Corporation Method for improving the dyeing characteristics of textile materials containing polyolefin fibers and products produced thereby
WO1996001916A1 (en) * 1994-07-12 1996-01-25 Lyondell Petrochemical Company Wettable polyolefin fiber compositions and method
US5614574A (en) * 1994-07-12 1997-03-25 Lyondell Petrochemical Company Wettable polyolefin fiber compositions and method
WO1999020817A1 (en) * 1997-10-22 1999-04-29 Deutsche Institute für Textil- und Faserforschung Stuttgart Method for producing aqueous liquor dyeable modified polypropylene threads and the use thereof
US6555038B1 (en) 1997-10-22 2003-04-29 Deutsche Institute Fur Textil - Und Faserforschung Stuttgart Method for producing aqueous liquor dyeable modified polypropylene threads and the use thereof
WO2022077534A1 (en) * 2020-10-13 2022-04-21 广东永畅兴精密制造股份有限公司 Colored synthetic fiber and preparation method therefor

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